If you aren't familiar with them, desert boots (also known as chukka boots) are an ankle-length boot, generally made from suede, calfskin or leather, with two or three eyelets and a crepe (or sometimes leather or rubber) sole. Below are the Clark's Originals Desert Boots, modeled after the British military-issue desert boots.
The boots were hugely popular in the late 1940s and 1950s as casual wear, and have now made a comeback - primarily with hipsters and those with hipster fashion sensibilities.
But why are they so popular, you might ask? Well, the obvious reason is that they look vintage, and present somewhat of a counter-cultural image, which is very "in" right now with hipsters and generally fashion-forward folk of all varieties. But beyond the fashion is the function.
I bought a pair of the Clark's yesterday, and I must say, they really live up to the hype! They are very comfortable, and from what I can tell, very durable. And this is true of most desert boots, not just the Clark's - the simplicity of the design and construction makes them less likely to wear out.
The higher-quality desert boots are made by stitching the two leather pieces down to the crepe sole. This makes for a much stronger attachment of the sole to the boot. Crepe soles have their own set of merits, which you can explore further on your own if you feel so inclined; I will satisfy myself by simply touting their comfort and durability.
The Bottom Line:
Hipsters wear desert boots for the vintage fashion and counter-culture image, as they do with most everything else in their wardrobe. However, they rejoice inside silently because this is one of those select instances where their fashion comes with an unsolicited side-order of function.
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